Fall 2000 - Chemistry 255 — Fall 2000 Exam III Name...

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Unformatted text preview: Chemistry 255 — Fall 2000 Exam III Name: Please read each question carefully and write your answers in ink (blue or black only). 1. Please provide the IUPAC name for the following molecules. (15 pts) a) OH unm H OH .b IIIH b) Cl Br 0) c1 ¢ OH 2. Draw the structures of the 2 possible constitutional isomers for an alkyne with the molecular formula C4H6. Provide the IUPAC names for the 2 isomers (20 pts) 3. Explain briefly and clearly why treatment of l-propanol with sodium bromide fails to give 1-bromopropane, but treatment with PBr3 succeeds? Use structures and mechanisms to support your answer. (15 pts) 4. Arrange the following species from best leaving group (A) to worst leaving group (C). Account briefly for why A is a better leaving group than B. (10 pts) Br' 1. HO' \/ \/ 5. Circle the elimination product that you think will most likely be formed in the following reaction. Provide a mechanistic rationale (mechanism with a brief description) to support your answer. (15 pts) 6. Provide the product(s) of the following reaction. Circle the mechanism type(s) that you believe the reaction proceeded by, El support this answer with two different, brief reasons. (20 pts) Br H20 Sn2 E2 Snl/El Reason #1: Reason #2: 7. Please provide the starting materials that are needed to produce the following products (10 pts): a) Br Brz heat b) SOCI2 C1 8. Please provide the reagents that are needed to produce the following products from the given starting materials (15 pts): a) WOH W b) C) 9. Please provide the product that will be produced in the following reactions (15 pts): a) MgBr b) El U03 2)S(CH3)2 0) H2 Pd 10. Propose a synthesis of A starting from B. Show all reagents, starting materials and products (will be more than one step — two steps would be best). (15 pts) \/\\\/\/\ A - product B - starting material EXTRA CREDIT (5 pts): Circle the compound below that would have the lowest boiling point. W WOH W 0H ...
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